1. Field of the Invention
The present invention describes polycyclic compounds having a gem bis(hydroxymethyl) structure which may be utilized for curing into various thermoplastic or thermosetting compositions. The compounds may also be reactive through retaining unsaturation within the molecule, may be saturated, or may be derivatized with a halogen or phosphite to obtain fire retardant properties.
2. Description of the Art Practice
Various tricyclic compounds are described in U.S. Pat. No. 3,470,248 issued Sept. 30, 1969 to Brotherton et al. The materials described in the Brotherton et al patent are stated to be useful in the resin art such as in the preparation of urethane polymers, polyamides and polyurethane polyurea elastomers. U.S. Pat. No. 3,787,371 issued Jan. 22, 1974 to Brinkmann et al discloses similar compounds which are stated to be useful in the formation of clear polyamides.
U.S. Pat. 3,317,469 issued May 2, 1967 to Feichtinger et al also discloses the use of materials similar to those in the Brotherton patent. Wagner et al in German OLS 2641662 published Mar. 23, 1978 also discloses tricyclodecane derivatives which have been functionalized. British Pat. No. 1,266,016 published Mar. 8, 1972 discloses tricyclodecane curing agent. Japanese published patent application No. 54-4992 published Jan. 16, 1979 naming Kaya as an inventor also describes polycyclic compounds.
An unpublished disclosure concerning such compounds is found in U.S. Pat. application Ser. No. 074,368 filed Sept. 10, 1979 which is the invention of the author of this patent. Additional work concerning such compounds is found in the disclosures of Fujikura et al Synthetic Communications Volume 6 No. 3 pages 199-207 (1976). Further disclosures of such technology concerning polycyclic compounds is found in Pruett, Ann. N.Y., Acad. Sci. Volume 295 pages 239-248 (1977).
Additional polycylic compounds are disclosed in OLS No. 2,200,022 published July 19, 1973 by Gierenz et al. Still further technology involving polycyclic compounds is found OLS No. 2,307,627 published Sept. 5, 1974 by Grau. OLS. No. 2,013,316 published October 1, 1979 by von Bornhaupt also discloses polycyclic derivatives having hydroxyl functionality.
German Pat. No. 934,889 granted Nov. 19, 1955 to Roelen et al discloses polyesters of certain polycyclic compounds. German Pat. No. 1,694,868 granted February 19, 1972 to Jellienk et al discloses the use of polycyclic polyhydroxyl functional compounds in the preparation of urethanes.
Polycyclics compounds which are used to prepare unsaturated esters such as with maleic acid are disclosed in OLS No. 1,916,287 dated Oct. 15, 1970 Kolbel et al.
Several additional polycyclic compounds are disclosed in OLS No. 2,200,021 laid open July 26, 1973, noting Vegemund as an inventor discloses additional polycyclic polyfunctional compounds.
Canadian Pat. No. 893,716 to Falbe issued Feb. 22, 1972 also discloses aldehydes manufactured from polycyclic compounds. Conjugated unsaturated compounds, which are polycyclic in nature, are described in U.S. Pat. 4,143,065 issued Mar. 6, 1979 to Hoffmann et al. Additional compounds of interest to chemists studying polycyclic materials is U.S. Pat. No. 4,146,505 issued Mar. 27, 1979 to Weber et al. Certain aldehydes of polycyclic compounds are also disclosed in British Pat. No. 734,030 published July 2, 1955. Canadian Pat. No. 867,229 also discribes the production of polycyclic polyols in an application published May 3, 1961.
Nyi in U.S. Pat. No. 4,140,724 describes certain polycyclic monoethers in a patent granted February 20, 1979. In U.S. Pat. No. 4,117,030 issued Sept. 26, 1978 to Nelson several additional polycyclic compounds having various functional groups are disclosed.
Even though substantial work has been done in the area of polycyclic compounds, it is not yet been recognized that superior properties may be obtained from the geminal bis(hydroxymethyl) structure on the polycyclic compounds of the present invention and, if desired, thereafter derivatizing said compounds to form fire retardant materials.
Throughout the specification in claims, percentages and ratios are given by weight and temperatures are in degrees of Celsius unless otherwise indicated. To the extent that each of the foregoing references is applicable to the present invention, it is specifically herein incorporated by reference and citation by the examiner is requested.